Privileged and Condemned
by IWontApologizeForWhoIAm
Summary: The Upper East Side had always felt like a fairytale and a nightmare. It was unpredictable, to say the least. Some had habits that made them destructive, while others had a past that made them bitter. Everyone knows you don't make it in or out of Manhattan without a few scars. In a matter of hours, they would all collide. Gossip Girl - The Next Generation.


The Next Generation on the Upper East Side.

Chapter 1

 **First Name Basis**

Alicia Humphrey had a lot of admirable qualities.

She always made sure the face she showed the world was perfect. But aside from her physicality, she was always kind, and polite, and never _ever_ a burden. But her one flaw was enough to threaten everything. Selflessness can be a flaw, even with the best intentions.

They were best friends. Even when one felt betrayed, or the other was insensitive. Alicia and Mila were best friends.

The upper east side had always felt like a fairytale and a nightmare. It was unpredictable, to say the least.

Though Serena van der Woodsen was somehow depicted as the golden girl who could have anyone move mountains for her, after Alicia, there wouldn't be left that meeting with the doctor holding a resentment she would carry until the end of time. Dan was never a fan of bad news. But when she needed him the most, he held their small family together, in their big apartment.

Alicia spent the last day of the holidays playing the guitar on the balcony of her room. The guitar was from her grandfather, Rufus, and it never failed her.

At lunch with her mother, she noticed she was beautiful, but unsatisfied. They had the same golden hair.

At home while her father wrote, she noticed he would only be angry when he was lacking inspiration. In that moment he was anything but. She liked to say she was her fathers daughter. They appreciated a lot of the same things.

She liked the way that the breakfast table would always overflow in their house, as Dan made waffles and the chef made everything else. She appreciated the silence in their lives, each and every moment where words felt unnecessary. So every now and then, she was grateful for her parents and the life that they gave her. After all, she was their only child.

Whether or not she was ready for what the year would bring, Alicia could feel it. It was something somewhere between troubled and exhilarating.

Mila Stevenson had always been a mystery of some sort. She was captivating, the type that caused daydreaming. Her hair was chocolate and her skin was olive. And she never questioned her intuition, because it was always right. Almost always.

She never needed a man in her life, but they seemed to chase after her anyway. They could never resist the secret in her eyes.

It's too bad she couldn't trade all the meaningless hook ups and one night stands for anything like a father to look up to.

Her mother made sure she had enough, but it never seemed enough.

Isla Stevenson loved her daughter, but still, it never seemed like enough.

They seemed to fight endlessly but without reason, a lot of the time. They were both like puzzles, pieces scattered and left around, never really made much sense until you put them all together. Like mother like daughter, after all.

Chuck and Blair were nothing short of king and queen of Manhattan. Their lives were documented and every last step was an important one.

But Henry Bass was a whole other story. A gentleman like his father, he embraced the privilege that was his name. He was a master at doing the right thing but also at doing the wrong thing. Just as both his parents were.

To him, the upper east side was no jungle, desert or trap. It was simply his home, everything he had known since he was born.

With his mother's charm and his fathers good looks, he was inevitably, a womaniser. Unfortunately for the girls on the Upper East Side, he was taken. The relationship had always felt fleeting, yet it had lasted. He cared about her, and she was his first. He had nothing else to compare it to, but when he looked at his parents together, then them together, something told him it wasnt extraordinary.

But they did everything right, so maybe it was good enough for now. Or maybe it wasnt.

Benjamin Bass was never one to boast about his heritage. Often referred to as the 'forgotten' son or 'lost' boy, attention was never his thing, but he got it anyway. Mistaken for shy, guarded and occasionally rude, but Benny was just looking to be something they didn't expect. He could be charming, but they expected it. He could be rebellious, so he did the opposite.

One second he would be the nerd and the next he would forget that he cared about anything.

He didn't know who he was, and neither did anyone else.

All he wanted was to be something other than his parents. One day, he would figure it out.

At 15, he still had time, anyway.

Arabella Archibald only ever went by Belle. She was known for her wit and her name, and she never took things too seriously. At least thats how it looked.

But she was also known for her other title; Henry Bass' girlfriend.

Together for what felt like forever, your first love at 14 is not something you ever forget. But there was always something missing, and even Belle could feel it. An intensity or fiery passion, she didnt know yet, and part of her wished that she would never find out. It was safe and comfortable and for her, that was enough.

Her father was a good father, but we all know Nate was always quite easily distracted. Since her mother passed away, it just felt like one after another would come, and just as quickly, they would go. The poor guy couldn't help it. It was the type of grief that haunted them, yet at times it was the only sense of warmth in their lives.

She was 6 years old, and it brought her and her father together. But then she was a teenager, and all it did was tear them apart.

Joshua Rodriguez, part of the new family in town. They were Mexican, and his father had got lucky with a successful chain of hotels back home, so they had been living the privileged since he was born. Just coming from the inner circle in Boston, the fresh start in New York couldn't have had him any less excited.

Sporty and aloof were usually his two main characteristics. But we would all be wrong if we didn't assume there was more to him than just that.

He was meant to be preparing for his new school, but instead he found somewhere to break in his new basketball. To him, the new year was unimportant, but it was catching up to him despite his denial.

Next up was recklessness at its finest. Lexi Rodriguez didn't have a care in the world. She might be the little sister, but that never stopped her from staying out later than her brother. Or sometimes she just didn't come home.

But she was never a stupid girl. She knew that alcohol destroyed her brain cells and that drugs would damage her organs. She did them anyway. Besides that, she also made a habit of hurting the people she loved.

An endless number of people in her life had attempted to 'fix' her, but she always insisted she was too far gone. Habit is hard to break, but most of the time it just takes the right person and a whole other type of commitment.

Lexi did not plan on changing for the city.

In a matter of hours, they would all collide.


End file.
